The Metaphysics Of Ebay

Gary Vaynerchuck, David Foster Wallace, Steve Jobs, and Eminem on Escapism, Convenience, and the Attention Economy

Escapism and convenience. Those are the two things human beings value most.” So says Gary Vaynerchuck, the world’s foremost social media guru.

Over the past couple years, I’ve become enamored with Gary Vee. I like his no-bullshit style, pragmatic message, and his overall read on modern culture.

To put it another way— I’m a follower. But is everything Gary Vee sells worth buying?

In this essay, I’ll offer my take on the metaphysics of ebay, the positive and dark nature of the smartphone era, and why Gary Vee is theee voice of 21st century media culture.

Gary Vaynerchuck Getty Images

Gary Vaynerchuk has been in the social media game seemingly from the beginning of the internet. He’s built a massive online following over the years by dropping F-bombs, proselytizing the virtues of the flip game, and speaking his truth.

Gary Vee is everywhere. He commonly tells his followers they must, “post thirty pieces of content a day” to gain traction. To that end, he clearly drinks as much kool-aid as he’s selling.

Gary Vee’s Vast Social Media Presence

A quick spin around the internet shows how Vaynerchuk posts seemingly non-stop on every social media platform: Facebook, Instagram, Twitter, Youtube, LinkedIn, Tik Tok, Snap Chat, Reddit, Gary Vee website, and VaynerMedia website.

How does Gary Vee do it?

Gary Vaynerchuck’s Super Power

By and Large, after you listen to a handful of his podcasts or videos — of which there are thousands— you’ll pick up Gary Vee’s life story.

He loves telling it. Born in the Soviet Union in the seventies, he immigrated to the US. His difficult childhood forged his exceptional resilience and entrepreneurial spirit.

Gary Vee was a self-proclaimed terrible student, but his mother instilled in him an unbreakable sense of self-esteem. The failures of his youth evolved into an almost inhuman ability to give-no-fucks.

The result is Gary Vee’s fearless mindset, his super power.

Yes, in reality, this fearless mindset is Gary Vee’s super power. To think about this another way, Gary Vee’s like Wolverine (of Marvel MCU fame).

Wolverine’s super power isn’t the metal claws— but his ability to heal extremely fast. If you know your Marvel mythology, you know Wolverine’s healing ability, is in fact, what made (and continues to make) the metal claws possible.

Image of Gary V and Wolverine by Kaila Yu

The Growth Mindset Ethos of Gary Vee

Gary Vee appears to understand the ever-changing landscape in the media game. He’s been around since the beginning of internet-relevancy, but never rested on his laurels as an early adopted of any given platform.

Instead Vaynerchuck displays a robust growth mindset regarding the caleidescope-nature of online media.

To clarify, growth mindset is a term coined by Stanford Psychologist Carol Dweck. In essence, Dweck theorized that there are two mindsets, fixed mindset and growth mindset.

To summarize, “fixed mindset” is when you praise or focus solely on the result. Fixed mindset gets ingrained in us when we’re told in our youth, “you are good at X.”

Meanwhile, “growth mindset” is when you praise or focus only the process involved. Correspondingly, growth mindset is ingrained when we’re told, “you worked hard at X.”

For example, an runner raised with a fixed mindset will only race those he know he can already beat, because the greatest measure of success is winning.

Meanwhile, a growth mindset individual will look for opponents who are faster and faster, because the greatest measure of success is trying — your effort.

“Two Mindsets” Decision Tree by Nigel Holmes

Lose Yourself

Vaynerchuck is clearly operating with a growth mindset. But to that end, it’s as if he’s “growth mindset about growth mindset.”

To illustrate, Gary Vee often claims that “the most important scene in movie history” is the climactic scene of 8 Mile. I know what you’re thinking yes, that 8 Mile, starring rapper Eminem.

Eminem as B-Rabbit in 8 Mile. Image courtesy of Universal Pictures

Vaynerchuck explains his theory this way. By preemptively exposing his weaknesses, Eminem leverages these weaknesses into strength, while simultaneously stripping his opponents of their power. The result, as we can see in the film, is that Eminem becomes invincible.

This growth-mindset-on-steroids ethos shines through in Vaynerchuck quotes like:

The truth is undefeated.”

“You must lean into your uniqueness.”

“Document don’t create. Because, it’s easier to create when you don’t have to think.”

B. r’er Rabbit?

Do you realize “The 24/7 News Cycle” has been a thing for a decade now? Perhaps you noticed that the jetwash of modern media culture has changed everything.

As most humans struggle for air in the constant churn of media, Gary Vee revels in the flotsam.

Gary Vee share’s his love of Eminem’s character B. Rabbit. But he might as well share with us the fable of Br’er Rabbit. Br’er Rabbit is the trickster of African tradition who survived on his wits, cunning and ability to find comfort and happiness in the thorny briar patch.

It’s apparent in some of his quotes that Gary Vee is someone who not only likes the media jetwash — but see’s its value at stripping away a lot of our cultural bullshit:

What the internet is doing is it’s exposing us.”

“The only thing you can do is speak your truth, with humility.”

“Your biggest source of unhappiness is the secret you are hiding.”

On one hand, that seems like straight forward and obvious advice. On the other hand, it flies in the face of media as we know it. It’s homespun, yet revolutionary.

Vaynerchuck also catches many perfectionists and procrastinators off guard by suggesting a phase shift from quality to quantity recommending we “devalue production value, and upvalue output.”

As noted above, he often says people “should be posting 30, 40, 50 times a day.”

Theoretically this process suggested by Vaynerchuck will self-select. In other words, if you can’t post that many times — and be inherently interesting as yourself — you will fail at the game. The game will flunk you out.


In other words, Vaynerchuk is trying to say that production “value” is dead. It has been replaced by “authenticity value.”

To think of this another way, Gary Vee’s approach could also be described as wabi-sabi. Wabi-sabi is the classic Japanese world view that can be summarized as the beauty of imperfection.

According to Richard Powell, “Wabi-sabi nurtures all that is authentic by acknowledging three simple realities: nothing lasts, nothing is finished, and nothing is perfect.”

This Is Water

I wrote down something Gary Vee once told influencers,

It’s more important to share your process of going through this, than giving advice.”

The way Gary Vee said “this,” instantly made me think about David Foster Wallace and his famous Kenyon College Commencement Address, “This Is Water.

If I’m sharing my thought process, I was struck by this question, “Is Gary Vee the cultural counterpoint to David Foster Wallace?” Are they a dyad in the Force?

Whereas Wallace wrestled with lament over the toil of adulthood, Vaynerchuk fills the daily grind with purpose and even excitement.

David Foster Wallace struggled with his search for authenticity. Gary Vaynerchuk sees authenticity everywhere, and teaches us we don’t need to struggle with that.

Wallace lived too inside his head. Vaynerchuk puts it all out there.

Wallace considered himself a TV addict, and struggled against it as a 12-stepper. Vaynerchuk embraces every new platform and fills the airwaves with his own face.

David Foster Wallace informed us that this, this, is water. Vaynerchuk provides a new way to swim, or at least avoid sinking.

I find both men elegant in their own way.

The Darkside of Tech

Despite the uplifting nature of Gary Vee, I would disobeying my truth if I didn’t address the one major problem I have with him.

My problem with Gary Vee has to do with the darkside of technology. You know what I’m talking about: the FOMO, the anxiety, the endless scrolling, and soul-sucking malaise caused by social media and excessive screen time, which is caused by how the tech industry is monetized by eye-ball hours.

We’re driven by dopamine. We’re bloodhounds for the next like. is no different, and here we’re also driven by money. Make no mistake, Gary Vee is part of the machinery.

On Rabbit Holes and Easter Eggs

I’d like to share a brief story (my truth) about why tech bothers me. A couple years ago, I found a huge piece of driftwood floating in the Mississippi River with the word “smart” chiseled into it. This piece of driftwood seemed like a text message from God or something.

I couldn’t stop thinking about it, especially after I realized the word smart has two meanings — intelligent and pain. That realization was a rabbit hole which lead me to the inventor of the smartphone, Steve Jobs, and an inquiry into the dark side of tech.

In short, there’s evidence Steve Jobs not only knew about this dual nature of the smartphone, but planted Easter Eggs (that famous Pixar trope) in his Stanford Address that warn against the dark side of tech.

Tristan Harris Vs Gary Vee

It was at that point I started following Tristan Harris. Harris is the former Googler who founded the Center For Humane Technology. He’s testified to Congress against the addictive perils of technology. He’s the reason your iPhone now alerts you after you spend a half hour on instagram.

To summarize Harris’ (probably lost) cause, he promotes self-awareness. Basically, tech designers are so slick they learned to remove obstacles and choice to just keep you on their app.

With this intention, things like unnaturally colorful screens, endless scrolling, automatic playback— all prey on our simple brains. Indeed, the simplest thing you can do to not get sucked in completely is install greyscale on your phone.

Basically, Harris’ argument is that our antique reptilian brains have zero fucking chance against the best and brightest minds of Silicon Valley. Not only that, it will only get worse as long as Silicon Valley is monetized by time spent on device.

That said, why did I call this a lost cause? Because in order for Harris to spread awareness about humane tech… he must use social media the exact way he warns against. That’s a paradox which Harris hasn’t solved.

Oh, and not to mention you got Gary Vee’s charming ass out here telling wannabe influencers to post 30, 40, 50 times per day!

Who’s Got The Better Secret Sauce for Time Well Spent?

To put this another way, Harris is an industry insider who suggests limiting your screen time or risk becoming something less than human. Meanwhile, Vaynerchuk is an industry insider who suggests using social media exponentially more in a way that showcases our humanity.

Both men are sharing the secret sauce, who’s right?

Is Tristan Harris the canary in the coal mine, or a Ludite? Is Gary Vee a genius, or a villain?

Is the tech genie out of the bottle regardless of who wants to stuff it back in? Are we in serious peril? Or do we just need to learn how to swim in this fucking water? Maybe it all comes down to how you define “time well spent?”

Escapism and Convenience

Gary Vee himself provides the two things he claims humans cherish most: escapism and convenience.

The escape he provides comes in the form of hope.

Because he’s everywhere on social media, he’s convenient.

Even though another video of his pops up in my instagram feed every ten minutes, and I know he’s part of the machine, I can’t deny that I just like Gary Vee. His videos always provide a jolt of optimism, pragmatism, and focus.

Of all the professional influencers on the internet, Gary Vee is the everyman’s pro. He’s a family guy, with a clean record, he’s into sports, baseball cards, and I like that he dreams of buying the Jets.

Gary Vee often talks about working in his parent’s liquor store for his entire twenties. Based on his experience of grinding away at brick and mortar retail, he routinely says everyone needs to be more patient.

Regardless of what age you are, (20’s, 30’s, 40's?) be patient. This is what I mean about escape and hope. I can be (should be) patient? In this culture?

Patience is so counterintuitive today that it’s refreshing!

Gary Vee also will tell you that, “back in HS, when you were terrified about that zit? You had it all wrong, because everyone else was worried about their own zits!”

Listening to Gary explain how social media works — while he also tells you to be patient — is soothing, to the soul. I don’t know why, but these little chestnuts of wisdom act like balm for the anxious mind.

Like many a guru, he makes you believe it’ll all be okay.

But then there’s the flip game.

What is The Flip Game?

If there’s one thing I like most about Gary Vee, it’s when he talks about the flip game. The flip game is a core feature of the Gary Vee experience.

What exactly is the Flip Game?

In brief, the flip game is the buying something at a lower price, and reselling (or flipping) it for a profit. Gary Vee’s recommends participating in the flip game as a way to build basic business experience.

I find the videos of Gary rummaging around for 80’s-era toys and coffee mugs at garage sales as entertaining as American Pickers. (And that comes from a guy who lives in the American Pickers’ hometown!)

In essence, Gary Vee shows you how to flip twenty or forty dollars worth of rummage sale purchases into hundreds of dollars every weekend by reselling them on ebay.

In reality, that type of extra money can mean a lot to people. It can make the difference between a stressful month end and a little breathing room. In theory, a few extra bucks in your pocket means less stress.

And since I personally believe mood is a zero sum game, less stress means more peace in general. I guess that’s the basic argument that money can in fact buy happiness.

With this short term benefit in mind, the real beauty of the flip game is that it also provides a long term play.

Can You Learn the Basics of Business In The Flip Game?

Simply put, Gary Vee’s theory is that as a seller on ebay, one can teach themselves the valuable basic lessons of business. These include:

  1. Becoming a subject matter expert.
  2. The basics of marketing (photos, writing advertising copy).
  3. Learning how to price product, and how markets works.
  4. Value propositions
  5. Negotiation.
  6. Learning about Shipping.
  7. Dealing with unhappy customers.
  8. Understanding profit margin.

Gary Vee will even tell you exactly how to sell things on ebay.

Go to ebay and search “coffee mugs” (for example), filter by “sold items” and “highest price. That’s how you set your price.””

It may be hard to believe, but you will find used coffee mugs that have sold for hundreds of dollars. And you’ll certainly find hundreds of mugs that sold for ten or twenty dollars.

Who knows, maybe you can learn enough about business in the flip game to someday slide your side hustle out to the front and center?

Coming Full Circle — I Get In On the Flip Game

You gotta admit, Gary Vee is admirable. He’s a regular guy who’s scaled his flip game into a media empire. He dreams of someday buying the New York Jets. (As a Chicago White Sox fan, I can appreciate his love for the knock around Jets.)

At the same time, Gary Vee is trying to teach everyone the type of life skills no kid learns in the classroom. Real business basics.

He’s even doing it in a way that might earn you a little walking-around-money. How do I know that?

Because as I have said, I’m a follower of Gary Vee. And yes, you guessed it, I got in on the flip game. And to be honest, when I say I got in on it, I mean I got very into it.

Learning And Earning: How to Make $1000 on the Side

To summarize, ebay flipping is when you re-sell items and perform retail arbitrage.

For example, my family has a lot of lightly used (if not frustratingly unused) stuff that ebay would like. I also stopped by a few thrift stores and learned that I have a knack for cleaning up old Air Jordan’s and reselling them.

It’s fun for me, and relaxing. In short, I enjoy the process. I actually enjoy the entire process much more than I thought I would.

As such, I can add this positive insight that even Vaynerchuck hasn’t mentioned, nor Tristan Harris, Steve Jobs, or David Foster Wallace. It’s an observation that doesn’t fight Harris’ platform about the perils of tech — but is slightly healthier use of ourtime for two key reasons.

The flip game is a new, better, source of internet-related dopamine fixes. I’ll explain:

  1. First of all, when you attack a thrift store or garage sale intending to find the one or two items worth reselling — it’s like an easter egg hunt for grown ups.
  2. Secondly, once you begin selling on ebay, you’ll have the same urge to check your phone as usual. But it will be to check views on your ebay posts. (That’s the escapism) This behavior contrasts, yet is similar to, behavior of Facebook, IG, Snap, Twitter, Tik Tok, and yes Medium.

The difference here is that, ebay isn’t open-ended. When you create interest on ebay, you make a sale. Done deal. Full stop.

You also get paid for your time in this process.

Sure certain influencers make unknown incomes off the internet. I’m under the impression that earning $1000 on Youtube is incredibly time-consuming and incredibly rare, requiring a million views. And yes, monetizing your artistic talent brings another type of satisfaction, while building skills.

But making $1000 on ebay is comparatively a cinch. In addition, you could argue that business deals are an art form. And certainly a skill set many artists sorely lack.

And I argue that working the ebay game, learning and earning while you stumble around the internet — is a healthier brand of dopamine, compared to the endless scroll of instagram (or aforementioned youtube).

If that doesn’t sound like a win-win scenario, and a way to make the most out of the smartphone era, I don’t know what is?

Your Most Essential Audience

Maybe everything I’m arguing about the deeper metaphysics of ebay doesn’t align perfectly with Gary Vee’s message. Gary would probably say he doesn’t give a fuck about the metaphysics of ebay. That’s ok. The metaphysics of ebay can be my lane.

But also, Gary Vaynerchuck knows his limits. It seems few people know thyself like Gary Vee does. To that end, he always chooses to focus on his strengths instead of his weaknesses. And that’s perhaps his greatest advice as we look for a road map into the future:

Current Society sells us on filling the gaps on our weaknesses. But all the upside is tripling down on your strengths.” — Gary Vee

In other words, don’t create, just document your process. And speak your truth to your most important audience — the one in the mirror.

Pattern recognition is the task of the Artist. This is the pattern recognition you’re looking for.

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